title: Regioselective synthesis of 1,4-di(organo)[60]fullerenes through DMF-assisted monoaddition of silylmethyl Grignard reagents and subsequent alkylation reaction.
abstract: Monoaddition of Grignard reagents, in particular tri(organo)silylmethylmagnesium chlorides, to [60]fullerene took place smoothly in the presence of dimethylformamide to produce (organo)(hydro)[60]fullerenes, C60R(1)H, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R(-), which was then alkylated to obtain 58pi-electron di(organo)[60]fullerenes, C60R(1)R(2), in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo)[60] fullerenes bearing the same or different organic addends on the [60] fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.
authors.affiliation: Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. matsuo@chem.s.u-tokyo.ac.jp
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Matsuo
authors.forename: Akihiko
authors.initials: A
authors.lastname: Iwashita
authors.forename: Yoko
authors.initials: Y
authors.lastname: Abe
authors.forename: Chang-Zhi
authors.initials: CZ
authors.lastname: Li
authors.forename: Keiko
authors.initials: K
authors.lastname: Matsuo
authors.forename: Masahiko
authors.initials: M
authors.lastname: Hashiguchi
authors.forename: Eiichi
authors.initials: E
authors.lastname: Nakamura